One of the many things that has bothered me about the criminal justice system is that there are no "grays." Everything is either criminal or non-criminal. Conduct that on one day is legally acceptable, even if perhaps sharp and unwholesome, on the next day will, if a penal statute goes into effect, be criminal and punishable by years in prison.

This fair-to-foul scenario is particularly troublesome in certain areas of white-collar law. On day one, for instance, conduct which exploits "loopholes" in the tax law may go from widely-practiced and legally-tolerated "tax avoidance" to now-prohibited and severely punishable "tax evasion." When this change from acceptable to criminal occurs by statute, there at least is some public notice and warning to potential wrongdoers, although such notice obviously never reaches many persons. When, however, the law, or potential law, changes overnight by an unpredictable or unexpected court decision or an indictment based on a novel theory of prosecution, the sudden changes to what is considered prosecutable is even more problematical.

I do not have any easy solution to this problem. We cannot expect the government to send out a hundred million notices that new criminal laws have been enacted (although we do, for instance, require financial institutions to notify all of their credit card customers of interest rate changes). Nor, of course, if such notices were sent, can we reasonably expect a hundred million people to read or understand them. Additionally, we do not want to prohibit prosecutors from imaginative use of legally permissible tactics to prosecute what is apparently morally wrong and harmful.

We should, however, in the sentencing area recognize that it is essentially unfair to punish a defendant as seriously for conduct that had previously been generally accepted or tolerated than for conduct clearly known at the time of the offense to be criminal. Under this theory, for instance, Michael Milken could reasonably be prosecuted, as he was in the late '80s, for essentially "parking" stock, an arguably "civil" violation never before prosecuted criminally, but could not reasonably be sentenced, as he was initially, to ten years in jail (later reduced upon a Rule 35 motion).

I have on a few occasions argued to a sentencing judge that she should give a less severe sentence because the defendant's conduct was at the time he committed it not widely known to be criminal or generally was not prosecuted. I have never been successful, at least to the extent a judge explicitly agreed (of course, judges often do not explicate their reasoning). I am aware of no case in which a court explicitly granted a departure or variance on these grounds (although there may well be some). Nor am I aware of any Sentencing Guidelines consideration of this issue.

The decision by arbitrator Paul Tagliabue in the National Football League's New Orleans Saints "bounty" case (In the Matter of New Orleans Saints Pay-for-Performance/Bounty, December 11, 2012) is interesting and relevant. See here. See also here. Tagliabue, the former National Football League commissioner and a lawyer, affirmed the findings of misconduct made by Commissioner Roger Goodell but vacated the disciplinary sanction for the four players involved, suspensions of from four games to one year. Tagliabue based his vacation on sanctions essentially on two grounds: first, that the players' actions were encouraged by the coaches and other officials of the Saints, and, second, that professional football had previously treated such conduct gently, if not tolerating it. Tagliabue strongly suggested that when an existing "negative culture" is addressed by strict prohibitions, the penalties for violations should be phased in.

I do not expect federal sentences to be "phased in" so that, for instance, a violation of a new law within two years of enactment be punishable by a sentence of up to two years, and thereafter by up to five, although I do not think such an idea is entirely far-fetched. I do hope, however, that in appropriate cases judges consider adjusting sentences downward when the conviction is based on new law or a new application of existing law, especially when the change caused a sudden prohibition of generally acceptable behavior in the prevailing culture, even a negative culture. Mr. Tagliabue's opinion will not, of course, be considered precedential in the criminal law, but application of its reasoning in certain criminal cases may be appropriate.